Water → 1-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzyl)pyrrolidine

HRID 1159396Notes

Reaction equation

HRID 1159396 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Si:6]([O:13][C:14]1[C:15]([F:22])=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[Si:6]([O:13][C:14]1[C:15]([F:22])=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 138616973-{[Tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzaldehyde

Product 1

HCID 686193431-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzyl)pyrrolidineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyrrolidine (6.8 mL, 82 mmol) was added to a solution of intermediate 32, 3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzaldehyde (16.7 g, 66 mmol) in dichloromethane (200 mL). The reaction mixture was cooled on ice bath, and sodium triacetoxyborohydride (17.4 g, 82 mmol) was added in portions under stirring. The reaction mixture was intensively stirred for 12 h at RT. Water (100 mL) was added. The organic layer was separated. The aqueous one was extracted with CH2Cl2 (2×100 mL). The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo to give the title compound (19 g, 94%, 60 mmol). 1H NMR data (DMSO-d6): 6.92-7.03 (m, 2H, H—Ar), 6.83-6.91 (m, 1H, H—Ar), 3.58 (d, 2H, J=1.7 Hz, Ar—CH2); 2.38-2.46 (m, 4H), 1.63-1.70 (m, 4H) 0.97 (s, 9H, t-Bu), 0.16 (s, 6H, 2CH3).

Workup

  1. temperatureThe reaction mixture was cooled on ice bath
  2. stirringThe reaction mixture was intensively stirred for 12 h at RT
  3. customThe organic layer was separated
  4. extractionThe aqueous one was extracted with CH2Cl2 (2×100 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-23325a5608b54831bf46bf1f947513ed
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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