tert-butyl N-(4-aminobutyl)carbamate → [4-(3,4-Dihydro-2H-pyrano[3,2-b]pyridin-4-ylamino)-butyl]-carbamic acid tert-butyl ester

HRID 1624316Notes

Reaction equation

[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.[C:12]([O:16][C:17](=[O:24])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])([CH3:15])([CH3:14])[CH3:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:12]([O:16][C:17](=[O:24])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[O:1][CH2:2][CH2:3]1)([CH3:15])([CH3:13])[CH3:14]

Participants

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamate

HCID 5049666Sodium triacetoxyborohydride

HCID 450796202,3-Dihydro-4H-pyrano[3,2-b]pyridin-4-one

Product 1

HCID 69296245[4-(3,4-Dihydro-2H-pyrano[3,2-b]pyridin-4-ylamino)-butyl]-carbamic acid tert-butyl esterYield 72%

Procedure

Reaction of 2,3-Dihydro-pyrano[3,2-b]pyridin-4-one (277 mg, 1.85 mmol) with (4-Amino-butyl)-carbamic acid tert-butyl ester (269 mg, 1.43 mmol) using general procedure B for reductive amination with NaBH(OAc)3 (605 mg, 2.86 mmol), followed by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 97:2:1 followed by 95:4:1) afforded [4-(3,4-Dihydro-2H-pyrano[3,2-b]pyridin-4-ylamino)-butyl]-carbamic acid tert-butyl ester (330 mg, 72%) as a pale yellow oil.

Sources & evidence

ORD record: ord-3d6af4abc7cb4bc1bfee1c5b61947549
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778967B2

Reaction notes

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