Sodium triacetoxyborohydride → HCID 58092734, compound

HRID 1807659Notes

Reaction equation

HRID 1807659 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:15]=[C:16]1[O:20][C@H:19]([C:21]([Cl:24])([Cl:23])[Cl:22])[N:18]2[CH2:25][CH2:26][CH2:27][C@@:17]12[CH:28]=[O:29]>ClCCCl.C(Cl)Cl>[OH:29][CH2:28][C@@:17]12[CH2:27][CH2:26][CH2:25][N:18]1[C@@H:19]([C:21]([Cl:24])([Cl:23])[Cl:22])[O:20][C:16]2=[O:15]

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 11492787HCID 11492787, compound

Product 1

HCID 58092734HCID 58092734, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (544 mg, 2.57 mmol) was added to (3R,7aR)-1-oxo-3-trichloromethyl-dihydro-pyrrolo[1,2-c]oxazole-7a-carbaldehyde (obtained as described in J. Org. Chem. 2006, 71(1), 97-102, 500 mg, 1.835 mmol) in DCE (4 mL). The RM was stirred 18 h at rt then taken up in DCM, the organic layer washed with water, dried over Na2SO4 and evaporated. The crude product was purified using a 20 g RediSep® silica gel column (eluent DCM to 10% MeOH in DCM) to give the title compound as a clear pale yellow oil.

Workup

  1. washthe organic layer washed with water
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-b7150478eb8b4896bb3c23bfd67b8587
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

Loading…