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Ammonium Chloride → (S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylate

HRID 710033
Notes
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Reaction equation

HRID 710033 reaction equation
[Li]CCCC.[C:6]([Si:10]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:11][CH2:12][C:13]#[CH:14])([CH3:9])([CH3:8])[CH3:7].CON(C)[C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:31].[NH4+].[Cl-]>C1COCC1>[Si:10]([O:11][CH2:12][C:13]#[C:14][C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:31])([C:6]([CH3:9])([CH3:7])[CH3:8])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 610226Silane, (1,1-dimethylethyl)diphenyl(2-propynyloxy)-HCID 6882981,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylateHCID 178418339Butyllithium

Product 1

HCID 86706745(S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylateYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an argon atmosphere, n-BuLi (10.3 mL, 2.64 N hexane solution) was added dropwise to a solution of t-butyldiphenyl(prop-2-yn-1-yloxy)silane (8.576 g) in THF (200 mL) at −78° C. over 10 minutes, and after stirring at room temperature for 50 minutes, the reaction mixture was added dropwise to a solution of (S)-t-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (5.01 g) in THF (200 mL) through a cannula and temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (500 mL) and, after extraction with AcOEt, the organic layer was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (5.36 g, colorless oil.)

Workup

  1. temperaturewas raised to room temperature over an hour
  2. extractionafter extraction with AcOEt
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-2a5341d7992c42738b741facc0a034e5
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181229B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes