Pyrrolidine → HCID 12001225, compound

HRID 503209Notes

Reaction equation

HRID 503209 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([CH:25]=O)=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:13]=[CH:14][CH:15]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([CH2:25][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 57556918HCID 57556918, compound

Product 1

HCID 12001225HCID 12001225, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 12a (80 mg, 0.15 mmol) and pyrrolidine (0.013 mL) in dichloromethane (10 mL) was stirred for 30 min at RT, then sodium triacetoxyboro-hydride (100 mg) was added to the reaction mixture at 0° C. The mixture was stirred for 12 hours at RT. The reaction mixture was quenched with water and the product was extracted with CH2Cl2 (3×40 mL). The combined organic layers were dried over anhydrous Na2SO4, the solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel using a 3:7 mixture of ethyl acetate and pet-ether as the eluent to afford compound 13a (40 mg, 68%) as a solid. Mp 192-194° C.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe product was extracted with CH2Cl2 (3×40 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography on silica gel using
  6. additiona 3:7 mixture of ethyl acetate and pet-ether as the eluent

Sources & evidence

ORD record
ord-572e2dbd5b6a4912bc1702f1bf450c45
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

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