Sodium Hydroxide → HCID 9946011, compound

HRID 2087004Notes

Reaction equation

HRID 2087004 reaction equation
C([BH3-])#N.[Na+].[CH3:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH2:19])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:11]=2.[OH-].[Na+]>CO.C(O)(C(F)(F)F)=O.O>[CH3:5][N:6]1[CH:18]2[CH:13]([CH2:14][C@H:15]([NH2:19])[CH2:16][CH2:17]2)[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:11]=2

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 10268849HCID 10268849, compound

Product 1

HCID 9946011HCID 9946011, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A freshly prepared solution of sodium cyanoborohydride (0.91 g, 14.48 mmol) in CH3OH (3.0 mL) was added dropwise to a 0° C. solution of (3R)-9-methyl-6-(phenylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-amine (1.02 g, 2.99 mmol) in TFA (7.5 mL), then stirred at room temperature for 3 hours. The reaction was diluted with H2O (40 mL) cooled to 0° C. and made basic by the addition of 50% NaOH. The reaction mixture was extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo to give a colorless foam which was recrystallized from CH3OH/EtOAc to give 0.19 g (19%) of (3R)-9-methyl-6-(phenylsulfonyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazol-3-amine as a colorless as a mixture of cis and trans isomers: mp 217.0-219.3° C.; MS m/z 343.2 (M++H).

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a colorless foam which
  7. customwas recrystallized from CH3OH/EtOAc

Sources & evidence

ORD record
ord-d6622bf5369d420e94a3f9017bbf5699
Source dataset
uspto-grants-2004_04
Patent number
US06727274B2

Reaction notes

Loading…