4,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane → HCID 117902617, compound

HRID 520775Notes

Reaction equation

HRID 520775 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([NH:12][P:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH2:9][CH:10]=[CH2:11].[CH2:27](B1OC(C)(C)C(C)(C)O1)C=C>>[CH3:27][C:10](=[CH2:11])[CH2:9][C@@H:8]([NH:12][P:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:14])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

3

Reactant 2

HCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 117902212HCID 117902212, compound

Product 1

HCID 117902617HCID 117902617, compoundYield 95%

Procedure

The title compound is synthesized and purified analogously to 4b [except allylboronic acid pinacol ester 1b (32 μL, 0.15 mmol) is used as the nucleophile instead of 1a], affording 4m (34.4 mg, 0.0952 mmol, 95% yield) as a white solid. The analytical data are fully consistent with those reported previously.13 1H NMR (400 MHz, CDCl3): δ 7.86-7.80 (2H, m), 7.76-7.70 (2H, m), 7.50-7.46 (1H, m), 7.44-7.38 (3H, m), 7.29-7.17 (7H, m), 4.78 (1H, s), 4.69 (1H, s), 4.40 (1H, dddd, J=16.4, 16.4, 8.4, 8.4 Hz), 3.32 (1H, br dd, J=8.0, 6.0 Hz), 2.62 (1H, dd, J=13.6, 7.2 Hz), 2.53 (1H, dd, J=14.0, 7.2 Hz), 1.58 (3H, s); HRMS Calcd for C23H25NOP [M+H]+: 362.16738. Found: 362.16649. [α]20D=+39 (c=1.2, CHCl3) for a 97.5:2.5 er sample. The enantiomeric purity was determined by HPLC analysis in comparison with authentic racemic material (Chiracel OD-H, 92:8 hexanes:i-PrOH, 0.8 mL/min, 220 nm): tR of 4m: 11 min (major) and 14 min (minor).

Workup

  1. customThe title compound is synthesized

Sources & evidence

ORD record
ord-d5b3fafd5482429b9623d5f8de7dffb8
Source dataset
uspto-grants-2016_05
Patent number
US09328061B2

Reaction notes

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