N-methyl-2-pyrrolidone → 3-Hydroxy-2,2-dimethylbutanoic acid

HRID 2080307Notes

Reaction equation

HRID 2080307 reaction equation
CN1CCCC1=[O:7].Cl.BrC1[CH:11]=[C:12]([CH:15]=[CH:16]C=1)[CH2:13]N.C(N(C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)[O:28][C:29](C)=[O:30].[Na+]>C(O)(=O)C>[CH3:16][CH:15]([OH:7])[C:12]([C:29]([OH:30])=[O:28])([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 27249803-Bromobenzylamine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 1529843-Hydroxy-2,2-dimethylbutanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 250 mL shaker vessel was added 2,6-dimethoxy-4-polystyrenebenzyloxy-benzaldehyde (DMHB resin) (10 g, 1.5 mmol/g, 15 mmol) and 150 mL of 1-methyl-2-pyrrolidinone (NMP). 3-Bromo-benzylamine HCl salt (17 g, 75 mmol), diisopropylethylamine (DIEA) (13 mL, 75 mmol), acetic acid (HOAc) (15 mL), and Na(OAc)3BH (19.1 g, 90 mmol) were then added. The resulting mixture was shaken at rt for overnight, and was then washed with NMP (150 mL×2), dichloromethane (DCM) (150 mL×2), MeOH (150 mL×2) and DCM (150 mL×2). The resulting resin was dried in vacuum oven at 35° C. for overnight to yield DMHB resin-bound 3-bromo-benzylamine (15 mmol).

Workup

  1. washwas then washed with NMP (150 mL×2), dichloromethane (DCM) (150 mL×2), MeOH (150 mL×2) and DCM (150 mL×2)
  2. customThe resulting resin was dried in vacuum oven at 35° C. for overnight

Sources & evidence

ORD record
ord-4f6e394a7b3e422486e444f0d412a4ba
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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