Acetic Acid → 4-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-ethyl-4-phenylazepane

HRID 11220Notes

Reaction equation

HRID 11220 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[BH4-].[Na+].[C:33](O)(=O)[CH3:34]>>[F:30][C:2]([F:29])([F:1])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][N:12]([CH2:33][CH3:34])[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 116261604-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane

Product 1

HCID 219731134-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-ethyl-4-phenylazepaneYield 56%

Procedure

Isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg), in glacial acetic acid (0.05 mL) was added sodium borohydride (2 mg) in two portions. After addition, the mixture was stirred at room temperature for overnight. The mixture was concentrated under vacuum. Then saturated sodium bicarbonate and dichloromethane was added to the mixture and the organic layer was separated. The aqueous layer was extracted with dichloromethane 2 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum to give the product as a clear colorless sticky oil (1.8 mg, 56% yield).

Workup

  1. additionAfter addition
  2. concentrationThe mixture was concentrated under vacuum
  3. additionThen saturated sodium bicarbonate and dichloromethane was added to the mixture
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with dichloromethane 2 times
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a45246cc5f84d0cb90ea4bcf20c2b8c
Source dataset
uspto-grants-2006_08
Patent number
US07098203B2

Reaction notes

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