Sodium borohydride → HCID 70530323, compound

HRID 355222Notes

Reaction equation

HRID 355222 reaction equation
[BH4-].[Na+].[Si:3]([N:10]1[C@@H:13]([S:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:12]([CH:34]=[O:35])[C:11]1=[O:36])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>O1CCCC1.C(OCC)(=O)C>[Si:3]([N:10]1[C@@H:13]([S:14][C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:12]([CH2:34][OH:35])[C:11]1=[O:36])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86737792HCID 86737792, compound

Product 1

HCID 70530323HCID 70530323, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cold (ice bath) suspension of NaBH4 (227 mg, 6 mmol) in tetrahydrofuran (20 ml) was added dropwise a solution of trans 1-(t-butyldimethylsilyl)-3-formyl-4-tritylthio-2-azetidinone (2.0 g, 4.1 mmol) in tetrahydrofuran (5 ml). The reaction mixture was stirred at room temperature for 30 min, then diluted with ethyl acetate and washed successively with cold 1N HCl and brine. The organic layer was dried (MgSO4) and evaporated in vacuo to give the title compound (2.0 g) (quantitative) as an amorphous solid. It was used in the next step without further purification. ir νmax (CDCl3): 1740 cm-1. 1Hmr (CDCl3)δ: 7.25 (15H, m), 4.30 (1H, d, J=2, H-4), 3.28 (1H, dd, J=11, J=3, H-1'), 3.0 (1H, m, H-3), 2.55 (1H, dd, J=11, J=3, H-1'), 2.2 (1H, m, O--H), 0.9 (9H, s, t-Bu and 0.22 ppm (6H, s, CH3).

Workup

  1. washwashed successively with cold 1N HCl and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-54e903352203461d86944eb392f5a726
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

Loading…