Allyl chloroformate → (R)-2-(allyloxycarbonylamino)-3-benzyloxy-1-propanol

HRID 1983945Notes

Reaction equation

HRID 1983945 reaction equation
[NH2:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].Cl[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:18]([O:17][C:15]([NH:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4])=[O:16])[CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 18052Allyl chloroformateHCID 516892Sodium BicarbonateHCID 141184082-Amino-3-(benzyloxy)propan-1-ol

Product 1

HCID 53805095(R)-2-(allyloxycarbonylamino)-3-benzyloxy-1-propanolYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-2-amino-3-benzyloxy-1-propanol (5 g, 27.6 mmol) in CH2Cl2 (250 mL) was treated with allyl chloroformate (3.2 mL, 30 mmol) and saturated aqueous NaHCO3 (250 mL) for 18 h. The organic layer was separated and concentrated in vacuo. Purification by chromatography eluting with 30% EtOAc/hexanes afforded 6.9 g (94%) of (R)-2-(allyloxycarbonylamino)-3-benzyloxy-1-propanol as an amorphous solid: 1H NMR (CDCl3) δ 2.56 (br s, 1H), 3.69 (m, 3H), 388 (m, 2H), 4.54 (s, 2H), 4.58 (d, 2H, J=5.6 Hz), 5.23 (dd, 1H, J=10.4, 1.1 Hz), 5.33 (dd, 1H, J=17.1, 1.1 Hz), 5.42 (m, 1H), 5.93 (m, 1H), 7.35 (m, 5H).

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. customPurification by chromatography
  4. washeluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-386e62c244b141e781ff458b4e54bf34
Source dataset
uspto-grants-2009_06
Patent number
US07541020B2

Reaction notes

Loading…