Methanol → (3S)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate

HRID 2199459Notes

Reaction equation

HRID 2199459 reaction equation
[NH2:1][C:2]1([C:14]([OH:16])=[O:15])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[CH2:3]1.S(Cl)(Cl)=O.[CH3:21]O>>[NH2:1][C:2]1([C:14]([O:16][CH3:21])=[O:15])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86730031(3S)-1-amino-3-(4-bromophenyl)cyclopentane-1-carboxylic acid

Product 1

HCID 69094601(3S)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate

Conditions

Temperature
70 °C

Procedure

To a heterogeneous mixture of (3S)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylic acid (I-1C, 14 g, 49.3 mmol) in MeOH (250 mL) was added thionyl chloride (36.0 mL, 493 mmol) dropwise over a period of 20 minutes at room temperature via an additional funnel (exothermic). The reaction mixture was placed in an oil bath and heated to 70° C. for 4 hours. The solvent was removed under vacuum, with the residue being dissolved in ethyl acetate (200 mL) and washed twice with 1N NaOH. The organic layer was then dried over Na2SO4 and concentrated to give 10.8 g of (3S)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate. HPLC retention time=0.68 min (Condition G); LC/MS M+1=298/300.

Workup

  1. customThe reaction mixture was placed in an oil bath
  2. customThe solvent was removed under vacuum, with the residue
  3. dissolutionbeing dissolved in ethyl acetate (200 mL)
  4. washwashed twice with 1N NaOH
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5892d0d37ade4bfbb7c950bc69676c9b
Source dataset
uspto-grants-2016_06
Patent number
US09359286B2

Reaction notes

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