Sodium Hydroxide → HCID 86598340, compound

HRID 1270417Notes

Reaction equation

HRID 1270417 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]1[C@H:13]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:12][N:11]2[CH2:24][C:25](=[O:28])[CH2:26][CH2:27][C@@H:10]2[CH2:9]1)=[O:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([C:6]([N:8]2[C@H:13]([CH2:14][C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH:16]=3)[CH2:12][N:11]3[CH2:24][C@@H:25]([OH:28])[CH2:26][CH2:27][C@@H:10]3[CH2:9]2)=[O:7])[CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 18449067HCID 18449067, compound

Product 1

HCID 86598340HCID 86598340, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of (3R,9aR)-2-[3,5-bis(trifluoromethyl)benzoyl]-3-(1H-indol-3-ylmethyl)-octahydro-2H-pyrido[1,2-a]pyrazin-7-one (5.6 g) in acetic acid (75 mL) was added sodium triacetoxyborohydride (6.78 g). The resulting mixture was stirred for one hour at room temperature then poured in water and basified with 2M sodium hydroxide (aq.). The formed precipitate was collected by filtration, washed with water, suspended in toluene and concentrated in vacuo to afford 3,5-bis(trifluoromethyl) phenyl-[(3R,7S,9aR)-7-hydroxy-3-(1H-indol-3-ylmethyl)-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (5.7 g). Rf 0.35 (CH2Cl2/MeOH 9:1) (compound 12).

Workup

  1. filtrationThe formed precipitate was collected by filtration
  2. washwashed with water
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d24e17890d947ddb4919619b3e76b90
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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