Lithium tri-s-butylborohydride → HCID 58845229, compound

HRID 1819290Notes

Reaction equation

HRID 1819290 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C@@H:9]2[C@H:4]([CH2:5][C@@H:6]([C:16]([OH:18])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[OH:1][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[C@@H:4]([CH2:5][C@@H:6]([C:16]([OH:18])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 69899055HCID 69899055, compound

Product 1

HCID 58845229HCID 58845229, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 17.3 g of (3S, 4aR, 8aR) 6-oxo-2-methoxycarbonyl-1,2,3,4,4a, 5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid (46 mmol) in 240 mL of tetrahydrofuran is added 106 mL if 1.0 M L-Selectride in tetrahydrofuran. The mixture is stirred for 1 hour at room temperature, then quenched with 130 mL of 1.4 M hydrochloric acid. The layers are separated and the aqueous phase extracted with 50 mL of tert-butyl methyl ether. The organic phases are combined and extracted with 75 mL of saturated aqueous sodium carbonate. The aqueous phase is washed twice with 30 mL portions of tert-butyl methyl ether then acidified to pH 1 with 6 M hydrochloric acid. The product is extracted into 75 mL of tert-butyl methyl ether. The organic mixture is dried with sodium sulfate, and concentrated to 8.17 g of yellow solid. The product is crystallized from 20 mL of tert-butyl methyl ether to provide 6.92 g of the title compound (59% yield).

Workup

  1. customquenched with 130 mL of 1.4 M hydrochloric acid
  2. customThe layers are separated
  3. extractionthe aqueous phase extracted with 50 mL of tert-butyl methyl ether
  4. extractionextracted with 75 mL of saturated aqueous sodium carbonate
  5. washThe aqueous phase is washed twice with 30 mL portions of tert-butyl methyl ether
  6. extractionThe product is extracted into 75 mL of tert-butyl methyl ether
  7. dry with materialThe organic mixture is dried with sodium sulfate
  8. concentrationconcentrated to 8.17 g of yellow solid
  9. customThe product is crystallized from 20 mL of tert-butyl methyl ether

Sources & evidence

ORD record
ord-1cbe4726ee744711a3f2381a8f6249c0
Source dataset
uspto-grants-2009_10
Patent number
US07601738B2

Reaction notes

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