(R)-4-Boc-(3-Hydroxymethyl)morpholine

Name: (R)-4-Boc-(3-Hydroxymethyl)morpholine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 215917-99-0
Cat. No. CS-W001900
Purity≥96%
MDL No.MFCD06799477

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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(R)-4-Boc-(3-Hydroxymethyl)morpholine|CS-W001900

Structure of 215917-99-0

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General Information

CAS No. 215917-99-0
Cat. No. CS-W001900
Purity ≥96%
MDL No. MFCD06799477
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₉NO₄
Molecular Weight 217.26
Synonym(s) tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate
SMILES OC[C@@H]1COCCN1C(=O)OC(C)(C)C

Description

(R)-4-Boc-(3-Hydroxymethyl)morpholine features a chiral morpholine core with a Boc-protected amine and a pendant hydroxymethyl group, enabling selective functionalization in asymmetric synthesis. The protected amine ensures stability during reaction sequences, while the hydroxymethyl moiety offers a handle for further derivatization. This scaffold is well-suited for medicinal chemistry campaigns requiring stereocontrolled construction of complex heterocycles.

Application

(R)-4-Boc-(3-hydroxymethyl)morpholine serves as a versatile chiral building block in medicinal chemistry, enabling efficient access to morpholine-containing scaffolds. The Boc-protected amine and pendant hydroxymethyl group offer orthogonal functionality for sequential transformations. It exhibits excellent bench stability and facilitates mild deprotection, supporting reliable downstream derivatization in peptide and small-molecule synthesis.

Synthesis

Route1
- 714971-27-4
- In-stock
  
  24424-99-5
- ~82%
- In-stock
  
  215917-99-0
References
- BRISTOL-MYERS SQUIBB COMPANY Patent: WO2005/58245 A2, 2005 ; Location in patent: Page/Page column 31-32 ; WO 2005/058245 A2
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  101376-26-5
- ~82%
- In-stock
  
  215917-99-0
References
- Gavai, Ashvinikumar V.; Fink, Brian E.; Fairfax, David J.; Martin, Gregory S.; Rossiter, Lana M.; Holst, Christian L.; Kim, Soong-Hoon; Leavitt, Kenneth J.; Mastalerz, Harold; Han, Wen-Ching; Norris, Derek; Goyal, Bindu; Swaminathan, Shankar; Patel, Bharat; Mathur, Arvind; Vyas, Dolatrai M.; Tokarski, John S.; Chiang, Yu; Oppenheimer, Simone; Hongjian, Zhang; Marathe, Punit; Fargnoli, Joseph; Lee, Francis Y.; Wong, Tai W.; Vite, Gregory D. Journal of Medicinal Chemistry, 2009 , vol. 52, # 21 p. 6527 - 6530

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 59
LogP 0.6146
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Morpholine compounds

Key Words

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(R)-4-Boc-(3-Hydroxymethyl)morpholine

CAS No. 215917-99-0

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