Ammonium Chloride → tert-butyl N-{[1-(hydroxymethyl)cyclopropyl]methyl}carbamate

HRID 1848348Notes

Reaction equation

HRID 1848348 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:13](O)=[O:14])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.B.[NH4+].[Cl-]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1([CH2:13][OH:14])[CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuran2×HCID 51340346Boc-amcp-OH

Product 1

HCID 11701224tert-butyl N-{[1-(hydroxymethyl)cyclopropyl]methyl}carbamateYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 1-(tert-Butoxycarbonylamino-methyl)-cyclopropanecarboxylic acid (3.23 g, 15.0 mmol) was dissolved in THF (50 mL) and cooled to −70 C. Borane tetrahydrofurane complex (1 M in THF, 22.5 mL, 22.5 mmol) was added at −70 C. The mixture was then stirred at 0 C for 2.5 h after which borane tetrahydrofurane complex (1 M in THF, 7.5 mL, 7.5 mmol) was added at 0 C. The mixture was stirred at RT for 1.5 h. Aq. NH4Cl (50 mL) was added at 20 C and the aqueous phase was extracted with EtOAc (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to afford (1-Hydroxymethyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (2.6 g) as an oil.

Workup

  1. temperaturecooled to −70 C
  2. additionwas added at 0 C
  3. extractionthe aqueous phase was extracted with EtOAc (×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-833b05acb8fe4cc9b10cc0e969cbb541
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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