(1R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid → tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

HRID 352178Notes

Reaction equation

HRID 352178 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14](O)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1512526(1R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 11962831tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamateYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R,3S)-3-t-Butoxycarbonylaminocyclopentanecarboxylic acid (229 mg, 1 mmol) was dissolved in THF (10 mL) and borane-THF (1.5 mL, 1M solution) was added drop-wise at 0° C. and stirred overnight at r.t. The reaction mixture was poured into ice-cold water (10 mL) and extracted with ethyl acetate (2×50 mL). The ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and evaporated to yield a semi solid (160 mg, 74%). ESMS (+): 216 (M+1)+, 250 (M+Cl)+.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. extractionThe ethyl acetate extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f7c219bba08b41ed81c5a133f6c417d9
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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