HCID 66679731, compound → HCID 66679067, compound

HRID 1753945Notes

Reaction equation

HRID 1753945 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:19])[CH:16]=3)[N:11]([CH2:20][CH2:21][O:22]CC3C=CC=CC=3)[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]>CO>[CH2:30]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:19])[CH:16]=3)[N:11]([CH2:20][CH2:21][OH:22])[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:31]

Participants

3

Reactant 1

HCID 66679731HCID 66679731, compound

Product 1

HCID 66679067HCID 66679067, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 9-(2-benzyloxy-ethyl)-6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide (36) (600 mg, 1.4 mmol) in methanol (40 mL) was added a slurry of Pd/C_(100 mg) in methanol (5 mL). The mixture was placed on the Parr hydrogenator and shaken for 24 h under a hydrogen atmosphere. The reaction was filtered through a pad of celite, washed with methanol and concentrated in vacuo to afford 460 mg (80%) of 6-fluoro-9-(2-hydroxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide (37) as a yellow oil which was used in the next step without purification. The structure was confirmed by 1H NMR (300 MHz, MeOD-d3) δH 1.18 (3H, t, J=9 Hz, N(CH2CH3)2), 1.35 (3H, t, J=9 Hz, N(CH2CH3)2), 1.80-2.20 (4H, m, 2- and 3-CH2), 2.69-3.88 (2H, m, 1-CH2), 3.40-3.86 (6H, m, N(CH2CH3)2 and NCH2CH2OH), 4.03-4.22 (3H, m, NCH2CH2OH and 4-CH), 6.75-6.95 (2H, m, NCCHCHCFCH), and 7.05-7.15 (1H, m, NCCHCHCFCH.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-894d741eae6948398c149b1e58ef3600
Source dataset
uspto-grants-2015_10
Patent number
US09168317B2

Reaction notes

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