Acetic Acid → HCID 86649529, compound

HRID 1807662Notes

Reaction equation

HRID 1807662 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.[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH2:35].C(O)(=O)C>ClCCCl>[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH:35][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

6

Reactant 4

HCID 176Acetic AcidHCID 668533-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 11492787HCID 11492787, compound

Product 1

HCID 86649529HCID 86649529, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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), 3-fluorobenzylamine (0.251 mL, 2.20 mmol) and acetic acid (0.263 mL, 4.59 mmol) in DCE (4 mL) under an argon atm. The RM was stirred at rt for 3 h, then partitioned between water and DCM, the combined organic dried over Na2SO4 and evaporated to give the title compound as a pale yellow oil which was used without further purification.

Workup

  1. custompartitioned between water and DCM
  2. dry with materialthe combined organic dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-97ba1e0c03064fc7a5fa3ad75922137b
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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