HCID 86701036, compound → 1,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamate

HRID 1427659Notes

Reaction equation

HRID 1427659 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C>C(Cl)Cl>[OH:8][CH2:9][CH2:10][C:11]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:12][CH2:13]1

Participants

3

Reactant 1

HCID 86701036HCID 86701036, compound

Product 1

HCID 129931391,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamateYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropylcarbamate (11.9 g, 37.8 mmol) and 3HF.TEA (22.0 g) in DCM (50 mL) was stirred at rt for 17 hrs. The mixture was concentrated and the residue was purified by silica gel column chromatography (0˜20% gradient elution EtOAc/petroleum ether) to afford tert-butyl 1-(2-hydroxyethyl)cyclopropylcarbamate (4.6 g, 60%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (0˜20% gradient elution EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-4df83041561b4c7a9628c825ba8285b9
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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