Diisopropylethylamine → HCID 58043112, compound

HRID 1035235Notes

Reaction equation

HRID 1035235 reaction equation
[CH:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[CH:5][C:4]=1[CH3:21])=O.[CH3:22][C:23]1([CH2:29][OH:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:30][CH2:29][C:23]1([CH3:22])[CH2:28][CH2:27][N:26]([CH2:1][C:3]2[CH:20]=[CH:19][C:6]([O:7][CH:8]3[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]3)=[CH:5][C:4]=2[CH3:21])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22507737(4-Methylpiperidin-4-yl)methanolHCID 58043133Tert-butyl 3-(4-formyl-3-methylphenoxy)azetidine-1-carboxylate

Product 1

HCID 58043112HCID 58043112, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 69A (3.00 g, 10.3 mmol) in DCM (50 mL) was added (4-methylpiperidin-4-yl)methanol (2.56 g, 15.5 mmol) followed by DIPEA (3.60 mL, 20.6 mmol). The reaction mixture was stirred at RT for 20 min and then sodium triacetoxyborohydride (6.55 g, 30.9 mmol) was added. The mixture was stirred at RT overnight and then washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted several times with DCM. The organic layers were filtered through a phase separator and then evaporated. There was obtained 3.1 g (74%) of the product as an oil. 1H NMR (500 MHz, CDCl3): δ 0.95 (s, 3H), 1.33 (m, 2H), 1.45 (s, 9H), 1.51 (m, 2H), 2.26 (m, 2H), 2.30 (s, 3H), 2.51 (m, 2H), 3.38 (s, 2H), 3.39 (s, 2H), 3.99 (m, 2H), 4.27 (m, 2H), 4.84 (m, 1H), 6.48 (dd, 1H), 6.56 (d, 1H), 7.16 (d, 1H), MS (APCI+) m/z 405 [M+H]+.

Workup

  1. stirringThe mixture was stirred at RT overnight
  2. washwashed with a saturated aqueous solution of Na2CO3
  3. extractionThe aqueous layer was extracted several times with DCM
  4. filtrationThe organic layers were filtered through a phase separator
  5. customevaporated

Sources & evidence

ORD record
ord-0beda5a5fd824ac3a2c4a13a2e3dd6f2
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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