Methanol → Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate

HRID 1022025Notes

Reaction equation

HRID 1022025 reaction equation
[C:1]([S:5](/[N:7]=[CH:8]/[C:9]1[N:17]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])=[O:6])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO>O>[CH3:3][C:1]([CH3:4])([S:5]([NH:7][CH2:8][C:9]1[N:17]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 89548949methyl 3-[(E)-tert-butylsulfinyliminomethyl]-5,6,7,8-tetrahydroindolizine-2-carboxylate

Product 1

HCID 86684449Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 238a (4.0 g, 12.8 mmol, 1.0 eq.), NaBH4 (2.9 g, 76.9 mmol, 6.0 eq.), and methanol (100 mL). The reaction mixture was stirred at room temperature for 1 h. After this time water (50 mL) was added to the reaction and the resulting mixture was concentrated under reduced pressure. The residue was extracted with dichloromethane (3×50 mL). The combined organic layer was evaporated under reduced pressure to afford 238b (3.9 g, 96%), which was directly used in next step without further purification. MS: [M-C4H10NOS]+ 192.3.

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (3×50 mL)
  4. customThe combined organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-282f7f7a7fef4c368f4a4258ffe8e795
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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