Acetic Acid → (3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

HRID 355177Notes

Reaction equation

HRID 355177 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[I-].[K+].[Si:17]([N:24]1[C@H:27]([CH2:28][C:29]([S:34][CH3:35])([S:32][CH3:33])[S:30][CH3:31])[C@@H:26]([C:36](=[O:38])[CH3:37])[C:25]1=[O:39])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(O)(=O)C>C(OCC)(=O)C.C(OCC)C>[Si:17]([N:24]1[C@H:27]([CH2:28][C:29]([S:34][CH3:35])([S:32][CH3:33])[S:30][CH3:31])[C@@H:26]([C@H:36]([OH:38])[CH3:37])[C:25]1=[O:39])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 14127274(3S,4R)-1-(t-butyl dimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

Product 1

HCID 13104625(3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-oneYield 84.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

K-Selectride® (3.64 ml of 0.5 M, 1.82 mmol) is added by syringe to a mixture of potassium iodide (126 mg., 0.758 mmol) and (3S,4R)-1-(t-butyldimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one (298 mg, 0758 mmol) in freshly distilled ethyl ether (8 ml) at room temperature. The resulting mixture is stirred at room temperature for 2.5 hours, then quenched by the addition of acetic acid (218 mg., 3.64 mmol). The resulting mixture is diluted with ethyl acetate (25 ml) and filtered through celite. Removal of solvents in vacuo gives an oil which is chromatographed on silica gel (ether:petroleum ether) to yield 252 mg of (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one. N.M.R. (R isomer, CDCl3 +D2O) δ4.15(dq,l), δ3.95(ddd,l,J=9.5,2.3), δ3.26(dd,l,J=8,2.3), δ2.37(m,2), δ2.16 (s,9), δ1.37(d,3,J=6,6), δ1.0(s,9), δ0.26(s,6).

Workup

  1. filtrationfiltered through celite
  2. customRemoval of solvents in vacuo
  3. customgives an oil which
  4. customis chromatographed on silica gel (ether:petroleum ether)

Sources & evidence

ORD record
ord-8542e1e41b2b4db1b02648d9d246f6c7
Source dataset
uspto-grants-1983_03
Patent number
US04378315

Reaction notes

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