4-(4-Fluorophenyl)piperidine → 1-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

HRID 279215Notes

Reaction equation

HRID 279215 reaction equation
[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH:12]=O)[CH2:5]1)[CH:2]=[CH2:3].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH2:12][N:24]2[CH2:25][CH2:26][CH:21]([C:18]3[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 27591364-(4-Fluorophenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 226244751-allyl-3-(RS)-formyl-4-(SR)-(cyclopropyl)pyrrolidine

Product 1

HCID 226244721-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidineYield 61.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1.8 g (10 mmol) of 1-allyl-3-(RS)-formyl-4-(SR)-(cyclopropyl)pyrrolidine and 2.68 g (15 mmol) of 4-(4-fluorophenyl)piperidine in 30 mL of dichloroethane at rt was added portionwise 6.36 g (30 mmol) of sodiumtriacetoxyborohydride. After stirring for 3 h at rt, the reaction mixture was partitioned between CH2Cl2 and sat'd K2CO3. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, ethyl acetate:hexanes, 1:3) to give 2.1 g of the title compound.

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, ethyl acetate:hexanes, 1:3)

Sources & evidence

ORD record
ord-f2f93066fb644903859a466072cb27f8
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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