Water → HCID 20063333, compound

HRID 1084457Notes

Reaction equation

HRID 1084457 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([C:18](Cl)=[O:19])=[C:16]([CH:21]([CH3:23])[CH3:22])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1.[BH4-].[Li+].O.C(OCC)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([CH2:18][OH:19])=[C:16]([CH:21]([CH3:22])[CH3:23])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 20063341HCID 20063341, compound

Product 1

HCID 20063333HCID 20063333, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of crude 2-(4-fluorophenyl)-4-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carbonyl chloride (21 g) in dry tetrahydrofuran (300 ml) was treated dropwise with a solution of lithium borohydride in tetrahydrofuran (26 ml; 2.0M) and the mixture stirred at room temperature for 18 hours. The reaction mixture was then treated dropwise with water (50 ml), diethyl ether (500 ml) and more water (200 ml) and the organic layer was separated, washed with water (200 ml) and brine (200 ml), dried over magnesium sulphate and evaporated to leave a yellow oil. This was triturated with a hot mixture of diethyl ether (200 ml) and n-hexane (400 ml) to give 2-(4-fluorophenyl)-3-hydroxymethyl-4-isopropyl-1-oxo-1,2-dihydroisoquinoline (13.7 g) in the form of a white solid, m.p. 157°-158° C. [Elemental analysis: C, 73.1; H, 5.7; N, 4.4%; calculated: C, 73.3; H, 5.8; N, 4.5%; NMR (in CDCl3): 1.55 (7H, d, J=8 Hz,), 3.65 (1H, sept, J=8 Hz), 4.4 (2H, s), 7.1-7.4 (4H, m), 7.5 (1H, t, J=8 Hz,), 7.7 (1H, t, J=8 Hz), 8.04 (1H, d, J=8 Hz), 8.5 (1H, d, J=8 Hz)].

Workup

  1. customthe organic layer was separated
  2. washwashed with water (200 ml) and brine (200 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto leave a yellow oil
  6. customThis was triturated with a hot mixture of diethyl ether (200 ml) and n-hexane (400 ml)

Sources & evidence

ORD record
ord-b756aca4fc714f16ac0a68b9d2d10e10
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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