Acetic Acid → HCID 69434731, compound

HRID 1266108Notes

Reaction equation

HRID 1266108 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([C@@H:19]5[CH2:24][NH:23][CH2:22][CH2:21][C@@H:20]5[N:15]4[CH2:14][CH2:13][CH2:12]3)[CH:18]=2)=[C:5]([C:25]([F:28])([F:27])[F:26])[CH:4]=1.[BH4-].[Na+].[C:31](O)(=O)[CH3:32]>>[CH2:31]([N:23]1[CH2:22][CH2:21][C@@H:20]2[N:15]3[C:16]4[C:11](=[CH:10][C:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=5[C:25]([F:28])([F:26])[F:27])=[CH:18][C:17]=4[C@@H:19]2[CH2:24]1)[CH2:12][CH2:13][CH2:14]3)[CH3:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59012632HCID 59012632, compound

Product 1

HCID 69434731HCID 69434731, compoundYield 81%

Conditions

Temperature
55 °C

Procedure

To a solution of (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) in acetic acid (0.28 mL) was added NaBH4 (30 mg, 0.80 mmol) in 2 portion in 10 min interval at 55° C. The reaction mixture was stirred for 15 h at 55° C. then quenched by addition of H2O. The aqueous solution was basified with 50% NaOH then extracted with CHCl3. The combined organic solution was dried over MgSO4, concentrated in vacuo. The residue was chromatographed (silica gel; CHCl3:MeOH 99:1-98:2) to give the title compound as a yellow oil (26 mg, 81%). 1H NMR (CDCl3, 300 MHz) δ1.21-1.35 (m, 3H), 2.05-2.30 (m, 5H), 2.53-2.78 (m, 6H), 2.98-3.07 (br, 1H), 3.08-3.18 (br, 1H), 3.27-3.42 (m, 2H), 3.43-3.57 (br, 1H), 3.88 (s, 3H), 6.83 (s, 1H), 6.86 (s, 1H), 7.04 (dd, J=8.8, 2.9 Hz, 1H), 7.20-7.26 (m, 2H) ppm. MS (CI, NH3): 417.1 (base, M+H).

Workup

  1. customthen quenched by addition of H2O
  2. extractionthen extracted with CHCl3
  3. dry with materialThe combined organic solution was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel; CHCl3:MeOH 99:1-98:2)

Sources & evidence

ORD record
ord-17535d6744a44448a2a36a7063b912ad
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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