Ammonia → HCID 57941060, compound

HRID 1437367Notes

Reaction equation

HRID 1437367 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C:9](=O)[C@@H:8]([F:13])[CH2:7]1)=[O:5])[CH3:2].[CH3:14][C@@H:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].N>ClC(Cl)C.C(O)(=O)C.CO.ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C@@H:9]([NH:22][C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])[C@@H:8]([F:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 6431891-Phenethylamine, (+)-HCID 5049666Sodium triacetoxyborohydrideHCID 57941052HCID 57941052, compound

Product 1

HCID 57941060HCID 57941060, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Ketone (b) (1.02 g, 5.4 mmol) in dichloroethane (24 mL) and acetic acid (1 mL) was treated with (R)-α-methyl benzylamine (0.88 mL) and sodium triacetoxyborohydride (2.2 g). After 4.5 hours, the reaction mixture was loaded onto a silica gel column packed in 0.5% (2M ammonia in methanol) in dichloromethane and eluted with 0.5-10% (2M ammonia in methanol) in dichloromethane to give an oil (1.2 g).

Workup

  1. washeluted with 0.5-10% (2M ammonia in methanol) in dichloromethane

Sources & evidence

ORD record
ord-c779d207459f402a98c5197854682c30
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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