Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate → tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

HRID 539969Notes

Reaction equation

HRID 539969 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12](OC)=[O:13])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[OH:13][CH2:12][C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 546046Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylateHCID 4148881Lithium borohydride

Product 1

HCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamateYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of methyl 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylate (1.2 g, 5.6 mmol) in tetrahydrofuran (10 mL) at 0° C. was added dropwise a solution of lithium borohydride (244 mg, 11.2 mmol) in tetrahydrofuran (10 mL) The reaction mixture was allowed to warm to room temperature and stirred at this temperature overnight. The reaction was quenched by addition of water (10 mL) and the resulting mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 0.8 g of the product (yield was 76.2%).

Workup

  1. customThe reaction was quenched by addition of water (10 mL)
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3965613a7bc948b996b16850d8fb5a03
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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