Hydrochloric Acid → (S)-(+)-3-Cyano-4-(2-methylbutyloxy)phenylboronic acid

HRID 651308Notes

Reaction equation

HRID 651308 reaction equation
[Li].[C:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C@@H:15]([CH3:18])[CH2:16][CH3:17])C(O)=O)#[N:3].[B:19](OC)([O:22]C)[O:20]C.Cl>C1COCC1>[C:2]([C:4]1[CH:5]=[C:6]([B:19]([OH:22])[OH:20])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C@@H:15]([CH3:18])[CH2:16][CH3:17])#[N:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 3028194Lithium2×HCID 54501986(S)-(+)-3-Cyano-4-(2-methylbutyloxy)benzoic acid

Product 1

HCID 53923893(S)-(+)-3-Cyano-4-(2-methylbutyloxy)phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The experimental procedure for the preparation of the lithium salt was as described in the preparation of compound 43. A solution of trimethyl borate (2.70 g, 0.024 mol) in dry THF (10 ml) was added dropwise to the lithium salt solution. The resultant mixture was allowed to warm to room temperature overnight whilst stirring and dilute hydrochloric acid was then added. The THF/water azeotrope was removed in vacuo and the remaining residue was dissolved in diethyl ether and washed with water until acid-free. The ether was dried (MgSO4) and removed in vacuo to leave a fawn solid.

Workup

  1. customThe THF/water azeotrope was removed in vacuo
  2. dissolutionthe remaining residue was dissolved in diethyl ether
  3. washwashed with water until acid-free
  4. dry with materialThe ether was dried (MgSO4)
  5. customremoved in vacuo
  6. customto leave a fawn solid

Sources & evidence

ORD record
ord-fafe30abe6ee4814819541f97cf2c224
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Reaction notes

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