HCID 178514592, compound → HCID 178511289, compound

HRID 397171Notes

Reaction equation

HRID 397171 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C@H:10]1[CH2:15][CH2:14][C@@H:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[N+]=[N-]>[Pd].CO>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C@@H:13]2[CH2:14][CH2:15][C@H:10]([N:6]3[CH2:7][CH2:8][CH2:9][C@H:5]3[CH2:4][NH2:1])[CH2:11][CH2:12]2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 178514592HCID 178514592, compound

Product 1

HCID 178511289HCID 178511289, compoundYield 140.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2S)-2-(azidomethyl)-1-[cis-4-(4-fluorobenzyl)cyclohexyl]pyrrolidine (45 mg), 10% Pd/C (10 mg, Aldrich) and 5 ml of methanol were hydrogenated for 16 hours at 50 PSI. The reaction was filtered through fiberglass filter paper under nitrogen. The filtrate was stripped to yield 58 mg of an amber oil as product. MS (ESI) detects 291 (M+H).

Workup

  1. filtrationThe reaction was filtered through fiberglass
  2. filtrationfilter paper under nitrogen

Sources & evidence

ORD record
ord-693a02aff6f74441bb03c9ea432ad4df
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

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