Pivalic acid → HCID 86744221, compound

HRID 1032449Notes

Reaction equation

C(B(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[N:24][CH:23]=[CH:22][N:21]=3)[N:18]=[C:17]([CH:26]([CH3:28])[CH3:27])[C:16]=2/[CH:29]=[CH:30]/[CH:31]([OH:41])[CH2:32][C:33](=[O:40])[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:11][CH:10]=1.C(O)(=O)C(C)(C)C.[BH4-].[Na+]>C1COCC1.CO>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[N:24][CH:23]=[CH:22][N:21]=3)[N:18]=[C:17]([CH:26]([CH3:27])[CH3:28])[C:16]=2[CH:29]=[CH:30][CH:31]([OH:41])[CH2:32][CH:33]([OH:40])[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Triethyl borane (7.5 ml, 7.5 mmol) was added via syringe to a solution of the β-keto ester (3.17 g, 6.8 mmol, Step F) and pivalic acid (0.069 g, 0.68 mmol) in THF (50 ml) under a dry air atmosphere. The resulting orange solution was cooled to -78° C. and MeOH (10 ml) was added, followed by NaBH4 (0.28 g, 7.5 mmol). The resulting effervescent solution was stirred at -78° C. for five hours. The reaction was quenched by slowly pouring into ice cold H2O2 (5 ml, 30%) and allowing to stir overnight. The reaction was partitioned between H2O and CHCl3. The organics were washed extensively with H2O, dried (MgSO4) and evaporated to give 2.65 g (84%) of a yellow foam which was used in the next step without purification.

Workup

customThe reaction was quenched
additionby slowly pouring into ice cold H2O2 (5 ml, 30%)
stirringto stir overnight
customThe reaction was partitioned between H2O and CHCl3
washThe organics were washed extensively with H2O
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-7aa19d365ffe4294994ca5860d8e0f23
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04957971

Reaction notes

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