Methanol → HCID 57934815, compound

HRID 1433147Notes

Reaction equation

HRID 1433147 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:21]([C:42]3[CH:47]=[C:46]([Cl:48])[C:45]([O:49][CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:44][C:43]=3[O:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[N:22][N:23]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:24]=2[C:25](OCC(C)C)=[O:26])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].CO>C(OCC)C.[OH-].[Na+]>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]2[C:21]([C:42]3[CH:47]=[C:46]([Cl:48])[C:45]([O:49][CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:44][C:43]=3[O:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[N:22][N:23]([S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)(=[O:33])=[O:34])[C:24]=2[CH2:25][OH:26])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 69065306HCID 69065306, compound

Product 1

HCID 57934815HCID 57934815, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of lithium aluminium hydride (1M in ether, 0.3 ml, 0.3 mmol) was added dropwise to a stirred solution of 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-5-isobutoxycarbonyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (90 mg, 0.11 mmol) [prepared by use of the lithiation chemistry in the preceding example] in anhydrous diethyl ether (2 ml) at room temperature, under a nitrogen atmosphere. The suspension was stirred 2 h then sodium hydroxide solution (1M, 3 drops) was added, followed by methanol (0.5 ml). The mixture was partitioned between water (30 ml) and ethyl acetate (2×20 ml), and the combined organic phases were dried over magnesium sulphate, then concentrated in vacuo to give 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (58 mg, 88%)

Workup

  1. customat room temperature
  2. customThe mixture was partitioned between water (30 ml) and ethyl acetate (2×20 ml)
  3. dry with materialthe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a15c1a0d0a7473aaf081ade7e2e3e9f
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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