HCID 59026098, compound → HCID 86616816, compound

HRID 639129Notes

Reaction equation

HRID 639129 reaction equation
[C:1]([C@H:3]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][C@H:4]1[C:15]([NH2:17])=[O:16])#[N:2]>CO>[NH2:2][CH2:1][C@@H:3]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][C@@H:4]1[C:15]([NH2:17])=[O:16]

Participants

3

Reactant 1

HCID 59026098HCID 59026098, compound

Product 1

HCID 86616816HCID 86616816, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve (3S,4R)-4-cyano-1-(phenylmethyl)-3-pyrrolidinecarboxamide (1.50 g, 6.55 mmol) in methanol (10 mL). Add NiCl 6H O (3.11 g, 13.1 mmol) followed by NaBH (0.99 g, 26.2 mmol) portionwise. The reaction was stirred for 2 hours, but it was not complete. Additional NaBH (0.5 g) was added and the reaction stirred another 1 hour. The solution was filtered through a plug of celite and washed with methanol. The solvent was evaporated under reduced pressure yielding a crude oil (1.51 g). LCMS: m/z 234.4 (MH+).

Workup

  1. stirringthe reaction stirred another 1 hour
  2. filtrationThe solution was filtered through a plug of celite
  3. washwashed with methanol
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1bde94b809e94503bab6b79b55e1f7bf
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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