Lithium borohydride → tert-butyl (4S,7S,10aS)-7-(hydroxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

HRID 529538Notes

Reaction equation

HRID 529538 reaction equation
[Li+].[BH4-].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:17][CH2:16][S:15][C@H:14]2[CH2:18][CH2:19][CH2:20][C@@H:21]([C:22](OC)=[O:23])[N:13]2[C:12]1=[O:26])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[OH:23][CH2:22][C@H:21]1[N:13]2[C@@H:14]([S:15][CH2:16][CH2:17][C@H:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:5])([CH3:4])[CH3:6])[C:12]2=[O:26])[CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68292140(4S,7S,10aS)-methyl 4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Product 1

HCID 68310946tert-butyl (4S,7S,10aS)-7-(hydroxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamateYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (2 M in THF, 1.57 mL, 3.14 mmol) was added dropwise to a 0° C. solution of (4S,7S,10aS)-methyl 4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (750 mg, 2.09 mL) in THF (8 mL). The reaction mixture was then stirred at rt overnight. The reaction mixture was cooled to 0° C. and carefully quenched by slow addition of saturated aqueous NH4Cl. After 10 min of stirring, the mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give tert-butyl (4S,7S,10aS)-7-(hydroxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (513 mg, 1.55 mmol, 74.2% yield) as a white solid. Anal. Calcd. for C15H26N2O4S m/z 330.4. found: 330.9 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customcarefully quenched by slow addition of saturated aqueous NH4Cl
  3. stirringAfter 10 min of stirring
  4. customthe mixture was partitioned between EtOAc and water
  5. customThe organic phase was isolated
  6. washwashed with saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-338ee642f41c4d8db30363fceb0c82fb
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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