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Sodium bis(trimethylsilyl)amide → 3-((3S,6S)-6-Cyclohexyl-3-hydroxy-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

HRID 579184
Notes
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Reaction equation

HRID 579184 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:23]#[C:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@H:11]1[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].CC1(C)[C@@]23C4(ON4S(=O)(=[O:47])C2)C[C@H]1CC3>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:23]#[C:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:8][C:9]=1[N:10]1[C@H:11]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:13][C@H:14]([OH:47])[C:15]1=[O:16])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 11075194(S)-(+)-(Camphorsulfonyl)oxaziridineHCID 666849233-((S)-2-Cyclohexyl-6-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 666847753-((3S,6S)-6-Cyclohexyl-3-hydroxy-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl esterYield 45.1%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-((S)-2-cyclohexyl-6-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (3.2 g, 7.97 mmol, 1.0 equiv) in THF (15.0 ml) was added NaHMDS (1.0 M in THF) at −78° C. and the resulting solution was stirred at −78° C. for 1.5 hours. To this solution was then added a solution of (S)-(+)-(camphorsulfonyl)oxaziridine (3.65 g, 15.94 mmol, 2.0 equiv) in THF (10 ml) and the reaction mixture was stirred at −78° C. for 3 hours. The reaction was quenched by addition of sat. NH4Cl aq. solution. The mixture was extracted with EtOAc and the combined organic layer was dried over Na2SO4, and concentrate. The residue was purified by silica gel column chromatography, (Et2O/DCM 5%˜40%) to give 1.5 g of the desired product (yield 45%). MS: 418 [M+H+]

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 3 hours
  2. customThe reaction was quenched by addition of sat. NH4Cl aq. solution
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined organic layer was dried over Na2SO4
  5. concentrationconcentrate
  6. customThe residue was purified by silica gel column chromatography, (Et2O/DCM 5%˜40%)

Sources & evidence

ORD record
ord-82dc0ee844dd4664bbdba16f1ac182fa
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040690B2

Reaction notes

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