tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Name: tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 158984-83-9
Cat. No. CS-M1347
Purity≥97%
MDL No.MFCD08275034

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate|CS-M1347

Structure of 158984-83-9

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General Information

CAS No. 158984-83-9
Cat. No. CS-M1347
Purity ≥97%
MDL No. MFCD08275034
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₉NO₃
Molecular Weight 249.31
Synonym(s) tert-butyl 6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
SMILES O=C(OC(C)(C)C)N1CC(C=C2)=C(C=C2O)CC1

Description

tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate features a hydroxylated dihydroisoquinoline core with a bench-stable tert-butyl ester protecting group. This moiety integrates readily into complex alkaloid scaffolds and serves as a key intermediate in the synthesis of bioactive isoquinoline derivatives. The hydroxy functionality enables direct functionalization or derivatization under mild conditions.

Application

tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate serves as a versatile intermediate in the synthesis of isoquinoline-based scaffolds, enabling efficient functionalization at the C6 position. The protected hydroxyl group offers stability and compatibility with standard coupling reactions, while the dihydroisoquinoline core facilitates downstream transformations such as oxidation to quinolines or derivatization via electrophilic substitution. Its bench-stable nature and ease of purification support scalable synthesis workflows in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  59839-23-5
- ~85%
- In-stock
  
  158984-83-9
References
- Ueno, Hiroshi; Yokota, Katsuyuki; Hoshi, Jun-Ichi; Yasue, Katsutaka; Hayashi, Mikio; Hase, Yasunori; Uchida, Itsuo; Aisaka, Kazuo; Katoh, Susumu; Cho, Hidetsura Journal of Medicinal Chemistry, 2005 , vol. 48, # 10 p. 3586 - 3604
Route2
- In-stock
  
  24424-99-5
- 63905-73-7
- ~93%
- In-stock
  
  158984-83-9
References
- Daiichi Pharmaceutical Co., Ltd. Patent: US6525042 B1, 2003 ;
Route3
- In-stock
  
  24424-99-5
- ~99%
- In-stock
  
  158984-83-9
References
- Merck Sharp and Dohme, Ltd. Patent: US5700809 A1, 1997 ; US 5700809 A

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 49.77
LogP 2.6854
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroisoquinoline compounds

Key Words

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tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

CAS No. 158984-83-9

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