Borane → Tert-butyl 2-(aminomethyl)thiomorpholine-4-carboxylate

HRID 57586Notes

Reaction equation

HRID 57586 reaction equation
[C:1]([CH:4]1[S:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)(=O)[NH2:2].B>C1COCC1>[NH2:2][CH2:1][CH:4]1[S:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 71113884Tert-butyl 2-carbamoylthiomorpholine-4-carboxylate

Product 1

HCID 71113883Tert-butyl 2-(aminomethyl)thiomorpholine-4-carboxylateYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 2-carbamoylthiomorpholine-4-carboxylate (2.46 g, 10 mmol) in THF (80 mL) was cooled to 0° C. A solution of borane in THF (1.0 M, 40 mL, 40 mmol) was added over 15 minutes via addition funnel and the mixture was stirred at ambient temperature for 72 hours. The reaction was quenched by dropwise addition of methanol/acetic acid (18 mL, 9:1 v/v). The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and sat. aqueous Na2CO3. The aqueous layer was extracted with ethyl acetate and combined extracts were washed with water, brine and dried over sodium sulfate. Removal of the solvent under reduced pressure afforded the crude desired material 2.11 g, which was used directly in the next step. MS (m/z): 233 (M+H)+

Workup

  1. customThe reaction was quenched by dropwise addition of methanol/acetic acid (18 mL, 9:1 v/v)
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and sat. aqueous Na2CO3
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwere washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a4c0034f2cd8476aa3344d047a692f99
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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