Triethylamine → HCID 67194341, compound

HRID 547800Notes

Reaction equation

HRID 547800 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@@H:7]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][NH:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>C1COCC1>[CH2:34]([O:33][C:31]([N:9]1[CH2:10][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:12][C@@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:22])[CH3:21])[CH2:8]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11175384(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-piperidine

Product 1

HCID 67194341HCID 67194341, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.50 g (1.4 mmol) (3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-piperidine and 0.15 g (1.5 mmol) triethylamine in 30 ml of THF was added dropwise a solution of 0.26 g (1.5 mmol) benzyl chloroformate in 2 ml of THF at 0° C. After completed addition, the mixture was allowed to warm to room temperature during 30 min. Quenching with a saturated aqueous solution of sodium hydrogencarbonate was followed by extraction with three portions of dichloromethane. The combined organic extracts were washed with brine and dried over sodium sulfate. Flash chromatography gave 0.62 g (90%) of the title compound as a colorless oil.

Workup

  1. additionaddition
  2. customQuenching with a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionwas followed by extraction with three portions of dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-cbdde159a0fd4a808185ae73bcf41d38
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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