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Acetic Acid → (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-N-(dicyclopropylmethyl)but-3-en-1-amine

HRID 932033
Notes
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Reaction equation

HRID 932033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:18]=[CH2:19])[C@@H:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH2:10])[CH:5]=[CH:6][CH:7]=1.[CH:20]1([C:23]([CH:25]2[CH2:27][CH2:26]2)=O)[CH2:22][CH2:21]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:18]=[CH2:19])[C@@H:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[NH:10][CH:23]([CH:25]2[CH2:27][CH2:26]2)[CH:20]2[CH2:22][CH2:21]2)[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 70721Dicyclopropyl ketoneHCID 5003444Sodium cyanoborohydride2×HCID 58573105(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine

Product 1

HCID 67999637(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-N-(dicyclopropylmethyl)but-3-en-1-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.0 g (6.84 mmol) of (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine (Example 115, Step E), dicyclopropyl ketone (7.54 mL, 68.4 mmol), and acetic acid (1.96 mL, 34.2 mmol) in methanol (25.0 mL) was added sodium cyanoborohydride (1.44 mL, 27.4 mmol) at rt. The resulting mixture was stirred at 50° C. for 2 days. Acetic acid (1.5 ml) and sodium cyanoborohydride (0.6 g) were added again and heating was continued overnight. 200 ml of ethyl acetate was added, and the organic layer was washed consecutively with K2CO3 solution and sat. NaCl solution, dried over K2CO3, filtered and the filtrate was concentrated under reduced pressure at 60° C. The mixture was purified by flash chromatography on silica gel (eluent: DCM/MeOH, 95/5) to give the title compound.

Workup

  1. temperatureheating
  2. waitwas continued overnight
  3. washthe organic layer was washed consecutively with K2CO3 solution and sat. NaCl solution
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure at 60° C
  7. customThe mixture was purified by flash chromatography on silica gel (eluent: DCM/MeOH, 95/5)

Sources & evidence

ORD record
ord-ee362d582942414d99f61cb8e7683373
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296736B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes