Methanol → HCID 68690078, compound

HRID 1296294Notes

Reaction equation

HRID 1296294 reaction equation
C[O:2][C:3](=O)[CH:4]([N:6]1[CH:15]([C:16](OC)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:20])[CH3:5].[Li+].[BH4-].CO>C1COCC1.C(Cl)Cl>[OH:17][CH2:16][CH:15]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:20])[N:6]1[CH:4]([CH3:5])[CH2:3][OH:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 68694119HCID 68694119, compound

Product 1

HCID 68690078HCID 68690078, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Isomer B of methyl 2-(1-methoxy-1-oxopropan-2-yl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (0.28 g, 0.96 mmol) in THF (9.8 ml) was added to a stirring solution of LiBH4 (2.0 M in THF, 0.58 ml, 1.2 mmol) in THF (1.5 ml). After refluxing for 1.5 h, the reaction was cooled to room temperature and quenched with 0.036 ml of water. Sodium hydroxide (1N, 0.072 ml) and then water (0.054 ml) were added. The reaction mixture was filtered through Celite, rinsing with THF. Evaporation of the filtrate afforded 0.32 g of crude product. Flash chromatography (SiO2, 0.5 to 10% MeOH in CH2Cl2) afforded pure product (0.20 g, 89% yield). MS (ESI) 236 (M+H).

Workup

  1. temperatureAfter refluxing for 1.5 h
  2. customquenched with 0.036 ml of water
  3. additionSodium hydroxide (1N, 0.072 ml) and then water (0.054 ml) were added
  4. filtrationThe reaction mixture was filtered through Celite
  5. washrinsing with THF
  6. customEvaporation of the filtrate
  7. customafforded 0.32 g of crude product

Sources & evidence

ORD record
ord-d735332c44514c60ad068800c3ddd22a
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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