Triethylamine → HCID 39246160, compound

HRID 642832Notes

Reaction equation

HRID 642832 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12](=[O:16])[C:13]([OH:15])=[O:14])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C>C1COCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C@@H:12]([OH:16])[C:13]([OH:15])=[O:14])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 43444877HCID 43444877, compound

Product 1

HCID 39246160HCID 39246160, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-35 °C

Procedure

A solution of 12.4 g (23.0 mmol) (1R)—B-chlorodiisopinocampheylborane in 50 mL THF was added dropwise within 30 min to a solution of 4.6 g (20.7 mmol) 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-propionic acid and 3.14 mL (23.0 mmol) triethylamine in 150 mL THF cooled to −35° C. and the reaction mixture was kept for 1 h at this temperature and for 4 h at RT. To complete the reaction a solution of 5.0 g (9.3 mmol) (1R)—B-chlorodiisopinocampheylborane in 50 mL THF was added and the reaction mixture was stirred overnight at RT. THF was removed i.vac. and the crude product (2.0 g) was reacted further without purification.

Workup

  1. additionwas added
  2. customTHF was removed i.vac
  3. customand the crude product (2.0 g) was reacted further without purification

Sources & evidence

ORD record
ord-bb74c025b7d049bd869924db75e8a0cc
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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