(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acid → (R)-(4-(5,6-Diaminopyridin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone dihydrochloride

HRID 931105Notes

Reaction equation

HRID 931105 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15]C[C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10].C([O:28]C(N1CCO[C@@H](C(O)=O)C1)=O)(C)(C)C>>[ClH:1].[ClH:1].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][O:28][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10]

Participants

3

Reactant 2

HCID 6559076(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Product 1

HCID 117966380(R)-(4-(5,6-Diaminopyridin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Procedure

The title compound was prepared by a method analogous to the one used for Intermediate 1, but using (R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid for Step 1. 1H NMR (400 MHz, CD3OD) δ 1.81-2.03 (m, 4H) 3.37-3.51 (m, 3H) 3.60-3.73 (m, 3H) 3.75-3.85 (m, 2H) 3.90-3.97 (m, 2H) 4.49 (dd, 1H) 6.40 (d, 1H) 7.73 (d, 1H).

Sources & evidence

ORD record
ord-25dbc536175d4666ae77a9ceddc09b5e
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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