Acetaldehyde → HCID 68972781, compound

HRID 1726262Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:23]3[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=3)[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Li]CCCC.[CH:35](=[O:37])[CH3:36].C(O)(C(F)(F)F)=O>CCOCC.C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:23]3[CH:28]=[CH:27][C:26]([CH:35]([OH:37])[CH3:36])=[CH:25][CH:24]=3)[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[O:18]2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 4-[2-(4-bromo-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 277) (742 mg, 1.61 mmol) in Et2O (20 mL) cooled to −78° C. was added BuLi (2.5M in Hexanes, 0.80 mL, 2.0 mmol) and the mixture was stirred at −10° C. for 1 hour. The mixture was cooled to −78° C., acetaldehyde (0.5 mL) was added and the mixture was warmed to room temperature and stirred for 30 minutes. Work-up and purification gave the desired substrate. To the substrate in CH2Cl2 (3 mL) were added H20 (2 drops) and TFA (1 mL) and the mixture was stirred at room temperature for 1 hour to afford 1-[4-(2-piperidin-4-yl-benzo[1,3]dioxol-2-yl)-phenyl]-ethanol as a pale yellow solid (170 mg, 32% over 2 steps) after basic work-up and purification.

Workup

temperatureThe mixture was cooled to −78° C.
temperaturethe mixture was warmed to room temperature
stirringstirred for 30 minutes
customWork-up and purification
customgave the desired substrate
stirringthe mixture was stirred at room temperature for 1 hour

Sources & evidence

ORD record: ord-ec850666093f4ff2b8307c81313ec96b
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

Loading…