Morpholine → Morpholine-4-carboxylic acid 1-benzyloxycarbonyl-2-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

HRID 22689Notes

Reaction equation

HRID 22689 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:17](OC2C=CC([N+]([O-])=O)=CC=2)=[O:18])[CH2:13][N:12]1[C:29](=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:17]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:18])[CH2:13][N:12]1[C:29](=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 207247432-[2-(4-Fluorophenyl)acetyl]-4-(4-nitro-phenoxycarbonyloxy)-pyrazolidine-1-carboxylic acid benzyl ester

Product 1

HCID 20724738Morpholine-4-carboxylic acid 1-benzyloxycarbonyl-2-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-[2-(4-Fluorophenyl)acetyl]-4-(4-nitro-phenoxycarbonyloxy)-pyrazolidine-1-carboxylic acid benzyl ester, 39, (462 mg, 0.882 mmol) is dissolved in dichloromethane (9 mL). Morpholine (770 μL, 8.82 mmol) is added and the reaction immediately develops a light yellow color. After stirring about 1.5 hours at room temperature, the reaction is diluted with dichloromethane (20 mL) and washed with a 5% solution of Na2CO3 (2×20 mL). The combined aqueous layers are extracted with dichloromethane (20 mL), the organic layers combined, washed with water, brine, and dried. The solvent is removed in vacuo to afford 414 mg of the desired product as a clear oil.

Workup

  1. customthe reaction
  2. washwashed with a 5% solution of Na2CO3 (2×20 mL)
  3. extractionThe combined aqueous layers are extracted with dichloromethane (20 mL)
  4. washwashed with water, brine
  5. customdried
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-29cd025b81dd4d60906017588b6e00a3
Source dataset
uspto-grants-2005_02
Patent number
US06849627B2

Reaction notes

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