Triisopropyl borate → (1S,2R)-4-[2-(tertbutyldimethylsilanyloxy)-1-ethyl-4-pyridin-3-yl-butoxy]benzeneboronic acid

HRID 380053Notes

Reaction equation

HRID 380053 reaction equation
Br[C:2]1[CH:28]=[CH:27][C:5]([O:6][C@@H:7]([CH2:25][CH3:26])[C@H:8]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.C([O:37][B:38](OC(C)C)[O:39]C(C)C)(C)C>O1CCCC1>[Si:18]([O:17][C@H:8]([CH2:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C@H:7]([CH2:25][CH3:26])[O:6][C:5]1[CH:27]=[CH:28][C:2]([B:38]([OH:39])[OH:37])=[CH:3][CH:4]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 57090865(3R,4S)-3-[4-(4-Bromophenoxy)-3-(t-butyldimethylsilanyloxy)hexyl]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 20692751(1S,2R)-4-[2-(tertbutyldimethylsilanyloxy)-1-ethyl-4-pyridin-3-yl-butoxy]benzeneboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the method as described in Example 5b) from (3R,4S)-3-[4-(4-bromophenoxy)-3-(t-butyldimethylsilanyloxy)hexyl]pyridine (0.71 g, Example 88a)), tertbutyl lithium (1.80 ml, 1.7M in hexanes) and tri-isopropylborate (0.74 ml) in dry tetrahydrofuran (25 ml). After work up, the residue was purified by column chromatography eluting with a gradient 0-25% ethanol in ethyl acetate to give the sub-title compound as a foam (0.41 g).

Workup

  1. customPrepared
  2. customAfter work up, the residue was purified by column chromatography
  3. washeluting with a gradient 0-25% ethanol in ethyl acetate

Sources & evidence

ORD record
ord-7f4c6df0e94448b585531d8259735e6a
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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