Triethylamine → Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate

HRID 500222Notes

Reaction equation

HRID 500222 reaction equation
ClC(OCC)=O.[CH2:7]([O:14][C:15]([NH:17][C:18]1([C:21](O)=[O:22])[CH2:20][CH2:19]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[BH4-].[Na+]>C1COCC1.O>[CH2:7]([O:14][C:15](=[O:16])[NH:17][C:18]1([CH2:21][OH:22])[CH2:20][CH2:19]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 22178711Benzyl (1-(hydroxymethyl)cyclopropyl)carbamateYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chloroformate (0.17 mL, 0.0018 mol) was added to a solution of 1-[(benzyloxy)carbonyl]aminocyclopropanecarboxylic acid (0.35 g, 0.0015 mol) and triethylamine (0.25 mL, 0.0018 mol) in THF (5.0 mL) at −10° C. The mixture was stirred at RT for 30 min., filtered, and washed with THF. Sodium tetrahydroborate (0.11 g, 0.0030 mol) in water (1.0 mL) was added to the filtrate at 0° C., and stirred at RT for 2 h. The reaction mixture was carefully quenched with 1N HCl, and extracted with EtOAc. The extract was washed with saturated NaHCO3, brine, dried over MgSO4, filtered, and concentrated to give the crude product (0.32 g, 97%). LCMS: (M+H)=222.0, (M+Na)=244.0.

Workup

  1. filtrationfiltered
  2. washwashed with THF
  3. stirringstirred at RT for 2 h
  4. customThe reaction mixture was carefully quenched with 1N HCl
  5. extractionextracted with EtOAc
  6. washThe extract was washed with saturated NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b80eea09ccb044f3a85ccfcda6144537
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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