Lithium borohydride → HCID 23000593, compound

HRID 1058335Notes

Reaction equation

HRID 1058335 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=2)[C:9]1=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:17][CH2:16][C:15]1[CH:14]=[CH:13][C:12]([Cl:18])=[CH:11][C:10]=1[CH2:9][OH:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 18672364HCID 18672364, compound

Product 1

HCID 23000593HCID 23000593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a stirred solution of 2-(tert-butoxycarbonyl)-7-chloro-3,4-dihydro-2H-isoquinolin-1-one (18.4 g, 64.38 mMol) in 50 mL of anhydrous tetrahydrofuran under inert atmosphere at 0° C. was added 2.0M LiBH4 in tetrahydrofuran (64.38 mL, 128.76 mMol, 2 eq). This was stirred at 0° C. for 1.5 hours, quenched with saturated ammonium chloride solution, then partitioned between ethyl acetate and water. The organics were dried(Na2SO4) and concentrated in vacuo. This afforded 2-(tert-butoxycarbonylaminoethyl)-5-chlorobenzyl alcohol as a clear colorless oil (hplc rt=3.21 min, method A; mass spec m/z=286.2).

Workup

  1. customquenched with saturated ammonium chloride solution
  2. custompartitioned between ethyl acetate and water
  3. concentrationconcentrated in vacuo
  4. customThis afforded 2-(tert-butoxycarbonylaminoethyl)-5-chlorobenzyl alcohol as a clear colorless oil (hplc rt=3.21 min, method A; mass spec m/z=286.2)

Sources & evidence

ORD record
ord-f24d5b9c90924dbe93f2b7d454fb12de
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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