Sodium borohydride → HCID 86722470, compound

HRID 718857Notes

Reaction equation

HRID 718857 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[N:15]=[C:14]4[CH2:17][CH2:18][CH2:19][CH:20]5[CH2:27][C:24]6([CH2:26][O:25]6)[CH2:23][CH2:22][C:21]5([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[C:13]4=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[N:15]=[C:14]4[CH2:17][CH2:18][CH2:19][CH:20]5[CH2:27][C:24]([CH3:26])([OH:25])[CH2:23][CH2:22][C:21]5([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[C:13]4=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86722471HCID 86722471, compound

Product 1

HCID 86722470HCID 86722470, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

rac-(2′R,4aS,12bS)-9-(4-fluorophenyl)-12b-(pyridin-2-ylmethyl)-2,4,4a,5,6,7,9,12b-octahydro-1H-spiro[benzo[3,4]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridine-3,2′-oxirane] (119, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (1.865 g, 4.10 mmol) was suspended in EtOH (41.0 mL). NaBH4 (0.776 g, 20.52 mmol) was added to the then the mixture was warmed to about 65° C. for about 2 h. The mixture was cooled then concentrated under reduced pressure. Water (50 mL) was added to the material then the solids were collected by filtration and dried the material was purified on silica gel (120 g) using a gradient from 0-10% MeOH in DCM. Product fractions were combined and concentrated under reduced pressure to yield rac-(3R,4aS,12bS)-9-(4-fluorophenyl)-3-methyl-12b-(pyridin-2-ylmethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[3,4]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-3-ol (120, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl, R3=Methyl) (1.87 g, 99%); LC/MS, method 2, Rt=2.65 min, MS m/z 457 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.42-8.35 (m, 2H), 8.28-8.26 (m, 1H), 8.18 (s, 1H), 7.62 (s, 1H), 7.46-7.37 (m, 3H), 7.05-7.02 (m, 1H), 6.58 (d, J=7.8 Hz, 1H), 4.10 (s, 1H), 3.70 (d, J=12.6 Hz, 1H), 3.56-3.49 (m, 1H), 3.44-3.32 (m, 1H), 2.91 (d, J=12.8 Hz, 1H), 2.66-2.53 (m, 2H), 2.15-1.80 (m, 3H), 1.70-1.59 (m, 2H), 1.53-1.30 (m, 2H), 1.16-1.14 (m, 2H), 0.92 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationthen concentrated under reduced pressure
  3. additionWater (50 mL) was added to the material
  4. filtrationthe solids were collected by filtration
  5. customdried the material
  6. customwas purified on silica gel (120 g)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f463e93d13f42dc99234d9208add46a
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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