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Acetaldehyde → rac-[(3S,4R)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-ethyl-amine

HRID 527492
Notes
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Reaction equation

HRID 527492 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:10]([NH2:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21](=O)[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.O.C(O)(=O)C>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C@H:10]([NH:20][CH2:21][CH3:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 177AcetaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 669409261-Benzyl-4-(4-fluorophenyl)pyrrolidin-3-amine

Product 1

HCID 58312649rac-[(3S,4R)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-ethyl-amineYield 44%

Reagents, catalysts & solvents 4

HCID 176
Acetic Acid
Solvent
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 38 g (141 mmol) rac-(3S,4R)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-ylamine, 7.12 g (162 mmol) acetaldehyde, 12.1 mL acetic acid and 44.7 g (211 mmol) sodium triacetoxyborohydride in 400 mL THF was stirred for 3 h at 0° C. and then warmed to room temperature. Water, Na2CO3 aq. and ethyl acetate was added. The organic layer was washed with brine, dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient formed from ethyl acetate, heptane and NEt3. The product containing fractions were evaporated to yield 18.5 g (44%) of the title compound as brown oil. MS m/e: 299.4 [M+H]+.

Workup

  1. temperaturewarmed to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica eluting with a gradient
  7. customformed from ethyl acetate, heptane and NEt3
  8. additionThe product containing fractions
  9. customwere evaporated

Sources & evidence

ORD record
ord-3a2cf161382648269e99f8a435b9104d
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346786B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes