Triethylamine → HCID 10882735, compound

HRID 625562Notes

Reaction equation

HRID 625562 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[C:9]([Si:13](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:12])([CH3:11])[CH3:10].CCN(CC)CC.N1CCCC1=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:13]([O:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 120252-PyrrolidoneHCID 94078tert-ButyldiphenylchlorosilaneHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 10882735HCID 10882735, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-5-(hydroxymethyl)pyrrolidin-2-one (10 g, 87 mmol) in CH2Cl2 (50 mL) was added tert-butylchlorodiphenylsilane (25.6 g, 93 mmol), Et3N (12.1 mL, 87 mmol) and DMAP (1.06 g, 8.7 mmol). The mixture was stirred at room temperature until the starting pyrrolidinone was completely consumed and then diluted with CH2Cl2 (50 mL) and washed with water (50 mL). The organic layer was dried (Na2SO4), filtered, evaporated in vacuo and the crude material was submitted to flash chromatography (silica gel; 30 to 100% of EtOAc/hexanes) to afford (S)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidin-2-one (22.7 g, 74% yield) as a colorless oil. LC-MS (M+H)+=354.58. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.69 (br s, 1H), 7.64-7.61 (m, 4H), 7.50-7.42 (m, 6H), 3.67-3.62 (m, 1H), 3.58-3.51 (m, 2H), 2.24-2.04 (m, 3H), 1.87-1.81 (m, 1H), 1.00 (s, 9H).

Workup

  1. customwas completely consumed
  2. additiondiluted with CH2Cl2 (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9ddcb6ef3e624ccab77e0784d27ed303
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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