3-Tert-butoxycarbonylamino-3-cyclobutyl-propionic acid → tert-butyl N-(1-cyclobutyl-3-hydroxypropyl)carbamate

HRID 445091Notes

Reaction equation

HRID 445091 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:14]1[CH2:17][CH2:16][CH2:15]1)[CH2:10][C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH:14]1[CH2:15][CH2:16][CH2:17]1)[CH2:10][CH2:11][OH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 223093383-Tert-butoxycarbonylamino-3-cyclobutyl-propionic acid

Product 1

HCID 68522076tert-butyl N-(1-cyclobutyl-3-hydroxypropyl)carbamateYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-tert-butoxycarbonylamino-3-cyclobutyl-propionic acid (0.300 g, 1.23 mmol) in THF (12 mL) was added BH3—SMe2 (1.70 mL, 3.33 mmol; 2.0 M solution in THF) at 0° C. After stirring at rt for 10 h, the reaction mixture was quenched with satd. NaHCO3, extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated in vacuo to afford (1-cyclobutyl-3-hydroxy-propyl)-carbamic acid tert-butyl ester (0.100 g); LC-MS [M+H]+ 230.0. The product is sufficiently pure for the next step and used for the next step without further purification.

Workup

  1. customthe reaction mixture was quenched with satd
  2. extractionNaHCO3, extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d274076be214a25869e1c66c64b66f2
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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